4-Bromoaniline → HCID 178510763, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromoaniline (6.4 g, 37 mmol) was placed into a three-neck reactor, and the reactor was flushed with argon for 20 min. 60 mL anhydrous toluene was added. After cooling to 0° C., trimethylaluminum (28 mL, 2.0M solution in toluene, 56 mmol) was added slowly to keep the inner temperature below 20° C. Over 0.5 h, the addition was completed. Ice bath was removed, and the reaction mixture was warmed to room temperature and then stirred for additional 2.5 hrs. A solution of 2-chlorobenzyl cyanide (8.4 g, 55 mmol) in 35 mL anhydrous toluene was added, and the reaction mixture was heated to 80° C. After 18 hrs, the reaction mixture was cooled to room temperature and poured over a slurry of silica gel in CHCl3/MeOH (4/1, 400 mL). After stirring for 30 min, the mixture was filtered and the residue was washed with a mixture of CHCl3/MeOH (4/1). The combined filtrates were concentrated in vacuo, and the resulting solid was washed with hexane to give a light pink solid (5.78 g, 48% yield).

Provenance & Evidence